N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester

Base Information

• Chemical Name: N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester
• CAS No.: 96867-09-3
• Molecular Formula: C₂₀H₂₈N₂O₅
• Molecular Weight: 376.453
• Mol file: 96867-09-3.mol

Synonyms:N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester

Chemical Property of N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester

There total 1 articles about N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.4%

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate (24498-31-5) + Cyclobutanecarbonyl chloride (5006-22-4) → Nε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysine methyl ester (96867-09-3)

Guidance literature:

With triethylamine; In dichloromethane; a) 0 deg C, 1 h, b) RT, 2 h;

DOI:10.1021/jm00146a014

Reference yield: 93.2%

Nε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysine methyl ester (96867-09-3) → N2-(Cyclobutylcarbonyl)-N6-[(phenylmethoxy)-carbonyl]-L-lysine (96867-10-6)

Guidance literature:

With sodium hydroxide; In methanol; a) 0 deg C, 1 h, b) RT, 64 h;

DOI:10.1021/jm00146a014

Reference yield:

Nε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysine methyl ester (96867-09-3) → 5(S)-<α-(cyclobutylcarbonyl)-L-lysyl>amino>-4-oxo-6-phenylhexanoyl-L-proline trifluoroacetic acid salt

Guidance literature:

Multi-step reaction with 6 steps

1: 93.2 percent / 1N NaOH / methanol / a) 0 deg C, 1 h, b) RT, 64 h

2: 86 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CH₂Cl₂ / 64 h / Ambient temperature

3: 77 percent / CrO₃, 35percent H₂SO₄ / acetone / 0.33 h / 0 °C

4: 63 percent / 1-hydroxybenzotriazole hydrate, Et₃N, dicyclohexylcarbodiimide / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 64 h

5: 84 percent / H₂ / 10percent Pd/C / 16 h / 760 Torr / Ambient temperature

6: 63 percent / H₂O / 7.5 h / Ambient temperature

With chromium(VI) oxide; sodium hydroxide; sulfuric acid; hydrogen; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; water; acetone;

DOI:10.1021/jm00146a014

upstream raw materials:

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate

Cyclobutanecarbonyl chloride

Downstream raw materials:

N₂-(Cyclobutylcarbonyl)-N₆-[(phenylmethoxy)-carbonyl]-L-lysine

2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane

2-(2-carboxyethyl)-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane